Welcome to YT!! And congratulations on your new baby!
1. My favorite pin brush is the Madan. If you go to the Yorkie Products for Sale forum there will be threads by YT member Mimimomo. She is a truly terrific vendor who sells Madan products for very reasonable prices. She has a new website but I can't recall it right now. Nother good brand is Chris Christenson - you can google the name for their website. These are a little more expensive but some prefer them over the Madan.
2. I think that varies a lot by pup - some are just more stubborn than others.
Keep at it and he'll adjust soon.
3. If you just need clippers for his bottom, the pads of his feet, etc., I highly recommend the cordless Wahl Peanut clipper. It's very small, portable, yet plenty powerful. This is a very small clipper, it's not meant to groom the entire body. I got mine from ebay.
Good luck!! Can't wait to see pics of your baby.
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He is your friend, your partner, your defender, your dog. You are his life, his love, his leader. He will be yours, faithful and true, to the last beat of his heart. You owe it to him to be worthy of such devotion. -- Author Unknown